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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL497
CHEMBL497
Compound Name CLIOQUINOL
ChEMBL Synonyms VIOFORM | ORALCER | IODOCHLORHYDROXYQUIN | CLIOQUINOL | QUIN-O-CREME | DOMEFORM-HC
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names DOMEFORM-HC | QUIN-O-CREME | VIOFORM | ORALCER
Molecular Formula C9H5ClINO

Additional synonyms for CHEMBL497 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES Oc1c(I)cc(Cl)c2cccnc12
Standard InChI InChI=1S/C9H5ClINO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,1 ...
Download InChI
Standard InChI Key QCDFBFJGMNKBDO-UHFFFAOYSA-N

Sources

  • British National Formulary
  • Gene Expression Atlas Compounds
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification
  • Withdrawn Drugs

Alternate Forms of Compound in ChEMBL


CHEMBL497

Molecule Features

CHEMBL497 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:N Parenteral:N Topical:Y Black Box:N Availability Type:Withdrawn

Withdrawal Information

Year 1973
Country United Kingdom; United States; Germany; France; Japan
Reason Neurotoxicity
Class Neurotoxicity

Mechanism of Action

Mechanism of Action ChEMBL Target References
Copper chelating agent Copper PubMed PubMed
Iron chelating agent Iron PubMed PubMed
Zinc chelating agent Zinc PubMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Lymphoma, Non-HodgkinD008228EFO:0005952non-Hodgkins lymphoma1ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma1ClinicalTrials
Hodgkin DiseaseD006689EFO:0000183Hodgkins lymphoma1ClinicalTrials
EczemaD004485HP:0000964Eczema3ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia1ClinicalTrials
Myelodysplastic SyndromesD009190EFO:0000198myelodysplastic syndrome1ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-CellD015451EFO:0000095chronic lymphocytic leukemia1ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-LymphomaD054198EFO:0000220acute lymphoblastic leukemia1ClinicalTrials

Clinical Data

ClinicalTrials.gov CLIOQUINOL
The Cochrane Collaboration CLIOQUINOL

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL497. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL2736 Metabotropic glutamate receptor 4 Homo sapiens 0.990
CHEMBL3687 Arachidonate 12-lipoxygenase Homo sapiens 0.928
CHEMBL5508 Dual specificity tyrosine-phosphorylation-regulated kinase 1A Rattus norvegicus 0.614
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.537

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL3687 Arachidonate 12-lipoxygenase Homo sapiens 0.992
CHEMBL5192 Botulinum neurotoxin type A Clostridium botulinum 0.987
CHEMBL2736 Metabotropic glutamate receptor 4 Homo sapiens 0.984
CHEMBL2285 ADAMTS5 Homo sapiens 0.938
CHEMBL3880 Heat shock protein HSP 90-alpha Homo sapiens 0.812
CHEMBL5508 Dual specificity tyrosine-phosphorylation-regulated kinase 1A Rattus norvegicus 0.627
CHEMBL4224 Dual specificty protein kinase CLK1 Homo sapiens 0.228

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
305.5 304.9104 3.2 0 33.12 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
2 1 0 2 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
2.32 7.23 4.17 2.47 2 13 0.76

Structural Alerts

There are 4 structural alerts for CHEMBL497. To view alerts please click here.

Compound Cross References

ATC D - DERMATOLOGICALS
D08 - ANTISEPTICS AND DISINFECTANTS
D08A - ANTISEPTICS AND DISINFECTANTS
D08AH - Quinoline derivatives
D08AH30 - clioquinol

G - GENITO URINARY SYSTEM AND SEX HORMONES
G01 - GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
G01A - ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
G01AC - Quinoline derivatives
G01AC02 - clioquinol

S - SENSORY ORGANS
S02 - OTOLOGICALS
S02A - ANTIINFECTIVES
S02AA - Antiinfectives
S02AA05 - clioquinol

D - DERMATOLOGICALS
D09 - MEDICATED DRESSINGS
D09A - MEDICATED DRESSINGS
D09AA - Medicated dressings with antiinfectives
D09AA10 - clioquinol

P - ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
P01 - ANTIPROTOZOALS
P01A - AGENTS AGAINST AMOEBIASIS AND OTHER PROTOZOAL DISEASES
P01AA - Hydroxyquinoline derivatives
P01AA02 - clioquinol

P - ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
P01 - ANTIPROTOZOALS
P01A - AGENTS AGAINST AMOEBIASIS AND OTHER PROTOZOAL DISEASES
P01AA - Hydroxyquinoline derivatives
P01AA52 - clioquinol, combinations

ChemSpider ChemSpider:QCDFBFJGMNKBDO-UHFFFAOYSA-N
PubChem SID: 104171297 SID: 11112285 SID: 124882179 SID: 124882180 SID: 144203967 SID: 144207489 SID: 170465019 SID: 17389542 SID: 24715134 SID: 26746922 SID: 85148761 SID: 855601
Wikipedia Clioquinol

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL497



ACToR 130-26-7
Atlas clioquinol
BindingDB 32188
Brenda 199741 42598 75652
ChEBI 74460
ChemicalBook CB7298550
DrugBank DB04815
DrugCentral 681
eMolecules 491690
EPA CompTox Dashboard DTXSID7022837
FDA SRS 7BHQ856EJ5
IBM Patent System 3C73A6534D779DD58E39363CED68C930
LINCS LSM-2186
Mcule MCULE-5389218452
MolPort MolPort-000-146-025
Nikkaji J5.432A
NMRShiftDB 30096614
PDBe CQL
PubChem 2788
PubChem: Drugs of the Future 56310601
PubChem: Thomson Pharma 14898627
SureChEMBL SCHEMBL3967
ZINC ZINC000006409735

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/QCDFBFJGMNKBDO-UHFFFAOYSA-N spacer
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